Water → 3-Butoxycyclobut-3-ene-1,2-dione

HRID 372627Notes

Reaction equation

HRID 372627 reaction equation
[OH:1][C:2]1[C:5](=[O:6])[C:4](=[O:7])[CH:3]=1.O>C(O)CCC.C1C=CC=CC=1>[CH2:5]([O:1][C:2]1[C:5](=[O:6])[C:4](=[O:7])[CH:3]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 962WaterHCID 40452Moniliformin

Product 1

HCID 157231823-Butoxycyclobut-3-ene-1,2-dioneYield 162.8%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 2631-ButanolSolvent

Procedure

A suspension of 1.25 g of 1-hydroxycyclobutene-3,4-dione (A) in 10 ml of absolute n-butanol and 15 ml of benzene is heated to reflux in a Soxhlet apparatus. A passes slowly into solution. The water of reaction is bound to the molecular sieve 4A which is present in the apparatus. The reaction mixture is concentrated after 2 hours. The distillation of the residue at 105°-115° C/0.01 Torr yielded 1.6 g (=82% of theory) of 1-n-butoxycyclobutene-3,4-dione as a yellowish oil.

Workup

  1. temperatureis heated
  2. temperatureto reflux in a Soxhlet apparatus
  3. concentrationThe reaction mixture is concentrated after 2 hours
  4. distillationThe distillation of the residue at 105°-115° C/0.01 Torr

Sources & evidence

ORD record
ord-444ec9eed4dc4b26a8eecdbacb90b5e6
Source dataset
uspto-grants-1978_05
Patent number
US04092146

Reaction notes

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